Sodium Carbonate → HCID 9967691, compound

HRID 983907Notes

Reaction equation

HRID 983907 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1C(O)=O)=O.Br[C:17](=[CH:23][C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1)[C:18]([O:20][CH2:21][CH3:22])=[O:19].C([O-])([O-])=O.[Na+].[Na+]>C(OC(=O)C)(=O)C.O.C(OCC)(=O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:8]2[C:9]([CH2:13][CH2:14][CH2:15]2)=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:23]=1[C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 714593117918-58-8HCID 86588967HCID 86588967, compound

Product 1

HCID 9967691HCID 9967691, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 7918Acetic AnhydrideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

N-(2-Thienylcarbonyl)proline (4.69 g, 21 mmol) is dissolved in acetic anhydride (15 ml) at 60° C. (15 min), ethyl 2-bromo-3-(4-pyridyl)propenoate (6.40 g, 25 mmol) is added to the clear solution and the mixture is heated at 90° C. for 16 h, whereupon a tlc sample (Al2O3-ethyl acetate/THF 9:1) no longer indicates starting material. The cooled reaction mixture is treated with ethyl acetate (120 ml) and intensively stirred with saturated Na2CO3 solution (80 ml) for 15 min and diluted with water (50 ml). The ethyl acetate phase is separated off, the water phase is extracted with a further 3 portions of ethyl acetate (150 ml), and these organic phases are combined, washed with saturated Na2CO3 soln (50 ml) and, after drying (K2CO3 sicc.), concentrated in vacuo. 8 g are obtained as a residue, which is dissolved in a little ethyl acetate and purified by cc (Al2O3-ethyl acetate/n-hexane 2:1).

Workup

  1. additionis added to the clear solution
  2. customThe cooled reaction mixture
  3. customThe ethyl acetate phase is separated off
  4. extractionthe water phase is extracted with a further 3 portions of ethyl acetate (150 ml)
  5. washwashed with saturated Na2CO3 soln (50 ml)
  6. dry with materialafter drying (K2CO3 sicc.)
  7. concentrationconcentrated in vacuo
  8. custom8 g are obtained as a residue
  9. custompurified by cc (Al2O3-ethyl acetate/n-hexane 2:1)

Sources & evidence

ORD record
ord-20a39d6190934ae3b07900f34d37d776
Source dataset
uspto-grants-2005_03
Patent number
US06867211B2

Reaction notes

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